


Jimmy, Jemma, and Cas

by rw_eaden



Category: Supernatural
Genre: (that's the one for non-binary people), Alternate Universe - Human, Alternate Universe- No Supernatural, Bisexual Dean Winchester, Bisexual Jimmy Novak, Castiel and Jimmy Novak Are Twins, Dick Jokes, Drag Queen Benny Lafitte, Drag Queen Jimmy Novak, Drag Queen Victor Henriksen, Drag Queens, Gender Related, Genderfluid Castiel, Implied/Referenced Exorsexism, Implied/Referenced Homophobia, M/M, Multi, Other, Pansexual Castiel (Supernatural), Pansexual Sam Winchester, Polyamory, Sassy Jimmy Novak, Shy Sam Winchester
Language: English
Status: Completed
Published: 2017-07-17
Updated: 2017-07-17
Packaged: 2018-12-03 07:36:46
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,369
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11527596
Author URL: https://archiveofourown.org/users/rw_eaden/pseuds/rw_eaden
Summary: Dean decides it's time for Sam to meet his partners. And, what better way to do that than to take Sam to one of his boyfriend Jimmy's drag shows?





	Jimmy, Jemma, and Cas

**Author's Note:**

> This was written for the [SPN Polybingo](https://spnpolybingo.tumblr.com/). The square was "gender fluid character".  
> Also, I should mention that characters refer to themselves as queer. If that's an issue, well, at least you know ahead of time. (I'm not sure how to tag the use of that word, but it's in the author's notes so now you know.)  
> Victor is Ivy Gene, Benny is Mama Belle Lafitte, and Jimmy is Ms. Jemma Sparkles. Insert your own headcanons for the other queens. :)

Dean steered Sam club by his shoulders, pushing him into the crowd and towards the table in the front of the theater that had been reserved specially for the two of them. It was one of only a handful of clubs that Dean actually enjoyed going to, and that was more to do with the fact that it wasn’t even really a nightclub. It was more of a comedy club/community theater house/drag show venue than anything else.

Sam scoffed in front of him. “You know I can walk by myself, right?” He asked, dragging his feet a little.

“Yeah, but you’re a much better battering ram than I am so, make like Moses and part this sea of people for me, yeah?”

Dean could practically hear Sam’s eye roll. “You could just say excuse me.”

“Or I could use you to make them move.”

Dean continued to steer them forward until they ran into the table they were supposed to sit at. It was Dean’s usual table, one that had been his since he’d started going to drag shows and long before he and Jimmy ever started dating. As usual, there was a small vase holding two red roses sitting in the center of the table. Sam smirked at him.

“Aren’t you supposed to bring him flowers?” Sam asked, taking his seat.

Dean rolled his eyes. “Please. I’ve gotten roses here since before we started dating. And, I told you, in here, you refer to Jimmy as Jemma and it’s she, by the way.”

“Sorry, I forgot.”

“No harm, no foul. Just don’t let any of the queens hear you. They might slap you.”

Sam laughed.

“You think I’m kidding.”

“No, no, I don’t,” Sam frowned, fiddling with the end of the table cloth, “But I still don’t see why you’re dragging me to this show to meet your partners.”

“You’ve never been to a drag show, Jemma’s a drag queen, Cas is gonna be here, it’s three birds with one stone. Practicality, Sam! I figured you’d be all over that!”

Sam squinted at him, “but you could have just invited me to dinner to meet them.”

Dean shrugged, a small smile pulling at his lips as Sam continued to frown. If Sam was implying that Dean had an ulterior motive, well, he wasn’t wrong. Everyone knew that your first drag show was a totally different experience, especially if you gave off that young, naïve, adorable vibe that Sam did. It wasn’t his fault, of course, he was just a twenty-something dude with shaggy hair and puppy dog eyes. And, Dean totally had to admit that Sam’s boyish charm had cute-d them out of several situations involving cops over the years. Drag queens, however, were a whole other thing. They all seemed to have some kind of radar that went off for prime embarrassment. Sweet, innocent little Sammy was going to be eaten alive and it was going to be glorious.

“We can have dinner after the show,” Dean said, “Cas usually wants pancakes anyway.”

“Where is Cas, by the way?” Sam asked.

Dean shrugged. “Probably in the back, like always.”

Sam opened his mouth to speak when a queen in a yellow dress came up beside him, her arms crossed over her chest. “Dean Winchester,” she said, “how the hell have you been?” Sam jumped.

“Hey, Ivy! Long time, no see!” Dean said, rising to his feet. Ivy practically smothered him in a hug before retreated, brushing her honey brown curls from her face.

“God, I know. I’ve been busting my ass at work recently,” she rolled her eyes. “Good news is I’m up for a promotion, so, lucky me.”

“Good for you. If anyone deserves it, it’s you.”

Ivy smiled and shrugged, her shoulders bouncing her spiral curls. “Who’s your friend?”

“Oh, this is my brother, Sam. It’s his first show,” Dean said. Sam gave a timid wave before reaching his hand out. The force with which Ivy shook his hand showed on his face and when he pulled back to massage his hand. Dean barely withheld a chuckle.

“Oooh! A virgin!” Ivy said, “the girls are going to have so much fun with you,” she winked at Sam.

Dean smirked as Sam shot him a questioning look, “Yeah, just don’t be too hard on him when you’re on stage. Poor thing turns so red you can see him from space if you poke him enough.”

Sam shot Dean a bitch face at that.

“Oh, don’t worry about me, hon, I’m just singing tonight. Besides, it’s Jemma you gotta worry about. She loves the cute ones.”

Sam’s bitch face shot up another level as he glared at Dean.

“Oh, trust me, I’m counting on it.” Dean winked at Ivy, then tried to give Sam something of an innocent smile, but he knew the smug delight was clear on his face.

Ivy let out a hearty laugh and shoved at Dean’s shoulder. “You’re kind of an asshole, you know that?”

“I’m allowed. It’s in the big brother contract. I have exclusive rights to be an asshole and embarrass the shit out of my little brother at any and all opportunities.”

“Well, Sam,” Ivy said, turning towards him, “you’re always welcome to come find me if he gets to be too much. I wouldn’t mind taking care of you.” Ivy cooed. A faint blush started to work it’s way up Sam’s cheeks. Ivy shook her head. “You’re right, Dean, he is too easy.”

Dean shrugged.

“Well, you too have fun. And try not to get too embarrassed, Sam. It’s all good fun.” And with that Ivy flitted off to talk to another table.

Dean sat back down and called the waitress over. Sam’s cheeks were still pink but he was scowling.

“You brought me here to embarrass me?” Sam asked.

“Would you believe me if I told you that she works for the police department? I mean, probably, ‘cause she’s got one hell of a grip.”

“Dean.”

Dean shrugged. “It’s a bonus more than anything, honestly. But, hey! Four birds with one stone! That’s like a record or something!”

“You’re an asshole. I should call Brady to pick me up.”

“Awh, Sam, don’t quit now. We aren’t even started yet! Besides, if you call your boyfriend to pick you up he’s probably just going to want to stay.”

Sam huffed and rolled his eyes. “Fine. But I’m getting you back for this.”

“Wouldn’t have it any other way,” Dean said.

The waitress came around then, taking their drink orders and walking away without another word. The lights began to dim them, and Dean scooted himself closer into the table. The conversations in the room dropped to hushed tones as the wait staff hurried to finish getting everyone their drinks and appetizers. The band ushered in, too, setting themselves at the drums, keyboards, and horns upstage.

A few moments later, the lights on the stage turned on and the MC for the night welcomed everyone to the show. His name was Chuck, and he the squirrelliest guy Dean had ever known. He also wasn’t very good in front of a crowd, so why he insisted on introducing every event made no sense to Dean.

The first act was a rendition of Donna Summer’s Bad Girls by a new girl named Layla Honey. Dean had seen her around once or twice but hadn’t really spoken to her before. She did a good enough job though, especially with the live band playing behind her. She sang something else that Dean was only half paying attention. He was much more focused on Sam, who seemed to be enjoying himself, which was good enough for Dean. He really did want Sam to have a good time, even if he was also looking forward to seeing him squirm under the attention he would undoubtedly get later.

The next two acts were musical numbers as well, on by a queen Dean had never heard of before and the other by Ivy Gene, the one performer Sam had met earlier that night. She’d pulled her hair up into an updo and had a simple diamond pendant around her neck. In the light on stage, Dean could see that her dress was actually more of a gold color, and it shimmered in the light. Dean was more than a little amused to see the way Sam’s eyes nearly bugged out of his head when she hit the high notes of I Will Always Love You. The crowd went wild as she moved around the stage with practiced ease, her head held high. She really did own the stage.  Dean made sure he and Sam both tipped her a little extra.

Sam started to squirm a little after Ivy left the stage, leaning over to whisper in Dean’s ear, “I swear the more I see her, I know that voice. Why do I know that voice?”

Dean snickered. “I’ll tell you later,” he said back, over the very appreciative crowd.

“Hey,” Sam asked, “is this a good time to bounce, ‘cause I have to pee.”

Dean glanced at his watch as Chuck stepped out to announce the next act. “Yeah, no. Intermission’s after this, so you’ll be good.”

And then Chuck announced Ms. Jemma Sparkles as the next act. Dean really couldn’t help the smile the spread across his lips even as Sam rolled his eyes.

Jemma walked out on stage, pretty much ignoring the audience at first. She was wearing a dark blue evening gown with a slit up the left leg, her black guarder clearly visible. Her long dark hair was curled at the ends and draped over a single shoulder. In her right hand, she had a glass of bourbon, which she drank from before even bothering to look at the audience.

The crowd, a little thrown off by the whole ordeal, sat there, whispering to themselves until someone in the back piped up “What are you gonna sing?”

Jemma rolled her eyes and snorted into the microphone. “Bitch, you want a song you get your ass up here and sing it yourself. Do I look like a trained parrot to you? Wait, don’t answer that.”

The crowd laughed, and Dean nudged Sam’s foot under the table. Sam rolled his eyes but he was laughing, too.

“Are you gonna sing?” Jemma rolled her eyes, wrenching the microphone from its stand, “no, I just planned on telling you to fuck off for twenty minutes until you gave me money.”

The crowd chuckled.

“Anyway, how the hell are you all?”

The crowd wooed.

“What the fuck was that? Woo? Woo is not an emotion, people. How the hell are you actually?”

There was then a muttered chorus of “good” and “fine” and a few enthusiastic “great’s” from the back.

“See, that’s better. How many drag virgins we got in the crowd tonight?”

A few hands went up here and there, but not Sam’s. He kept his eyes down. Dean coughed, kicking Sam under the table, but Sam kept his head down, squinting at Dean through his bangs. Dean rolled his eyes and coughed a little louder, just loud enough to get Jemma’s attention as he pulled Sam’s arm into the air. Sam looked up, blushing a bit and the smile Jemma gave the both of them was wicked.

“Hey there, cutie,” she said.

Sam flushed.

“Awh, this one’s shy,” she cooed.

There were a few chuckles in the crowd as she walked to the edge of the stage and sat down, swinging her legs over the edge. She battered her eyelashes at him, smiling sweetly.

“What’s your name cutie pie?”

“Sam,” Sam muttered.

“What was that?”

“Sam,” Sam said a little louder.

“Hi, Sam,” she cooed. Sam dipped his head. He was now closer in color to a tomato than a human, and Dean had to bite his lip to keep from laughing.

“Awh. God, I wish you in the back could see this. He’s positively adorable. I could just eat him up!” Jemma said, “Anyway, Sam, you said this is your first drag show?”

“Yeah, um, yes. It is.”

“How you likin’ it so far?”

“It’s good.”

“Having fun?”

“Yeah, yeah it’s good. Fun.”

“You don’t sound too convincing.”

“No, it’s fun. Really. I’m having a good time,” Sam said, scratching his neck as he let his eyes meet Jemma’s.

“You sure, ‘cause if you’re not having a fun time, I’m sure I could think of something that might make it more exciting. A strapping young man like you, I’m sure we could have all kinds of fun.” Jemma smirked, raising a single eyebrow.

The crowd whistled and catcalled. Dean snorted and Sam withered, tucking his face into his shoulder. Jemma laughed, jumping down off the stage.

“What about you, there in the back, the loud guy. Your first show?” Jemma asked.

Dean slipped her a twenty as she passed by.

“Yeah!” The same guy from earlier called out.

“What was your name?” Jemma asked.

“Dick!”

Jemma snorted. “You wish!”

Dean giggled. Sam, still a little embarrassed from earlier, reached for his drink and down half of it.

“Seriously, you go by Dick?”

The guy hollered out an affirmation and Jemma chuckled, flipping her hair back over her shoulder. “Honey, if you have to advertise…”

Whatever Dick said in response was drowned out by the crowd.

“Seriously, you don’t see me going by Candy Ass and I technically could.”

“It’s short for Richard,” someone else shouted out.

“Well no shit, of course, it is! If you keep calling yourself Dick people are gonna assume that!”

Jemma continued to rag on the audience for a while, cracking dirty jokes at their and her own expense. She moved through the crowd for a while, then eventually moved back towards the stage to finish her set. Sam had finally loosened up and was laughing along by the time the Jemma was finished and disappeared backstage.

The lights went back on for intermission, and Sam was finally able to get up and pee while Dean ordered them more drinks. By the time Sam came back, a few of the queens were walking around, greeting their friends and family members.

“So, what do you think, Sam?” Dean asked.

Sam frowned and poked at the ice in his whiskey sour with a stir stick. “You’re still an ass.”

“I’m still an ass but...”

Sam rolled his eyes. “It’s kinda fun.”

Dean slapped him on the shoulder. “Ha! I knew it! You’re having a good time.”

Sam tried to shoot him a frown, but he couldn’t keep the smile off his lips. “Yeah, well, aside from getting called out in front of the entire crowd.”

“Oh, come, on. You got off easy,” Dean said.

“Yeah, you could’ve been Dick,” a voice came from behind Sam. He jumped, turned to find Jemma smiling down at both of them.

“Hey, babe,” Dean said.

Jemma blew a kiss at him.

“You weren’t too embarrassed, were you Sam?” Jemma asked, frowning a little.

“Nah. It wasn’t too bad,” Sam shrugged.

“Be thankful I didn’t ask about band camp. Dean wanted me to bring that up for some reason,” Jemma said.

“Seriously, Dean? Band camp? That was like, ten years ago!” Sam squawked, kicking Dean in the shin.

Dean doubled over, clutching his leg. “Yeah, but it was funny. And it’s not my fault you thought you got your girlfriend pregnant from kissing her.”

“Shove it, Dean,” Sam said.

“Older siblings, right? We’re assholes,” Jemma said, setting her arm across Sam’s shoulders, her manicured nails digging into Sam’s left shoulder. “Now, I’m glad I didn’t ask.”

Sam smiled.

“Speaking of siblings, where’s Cas?” Dean asked.

Jemma frowned, whipping her head around a few times. “Fuck. I think I lost Cas. Sam, have you seen anyone that looks just like me but in a pink blouse?”

Dean snorted. “Babe, you look nothing like Cas, right now.”

Jemm rolled her eyes. “Okay. Like me but with a lot less eye shadow and a really short pixie cut?”

Sam shrugged.

“Crap. Well,” Jemma said, patting Sam on the shoulder, “if I don’t come back before intermission is up, just meet us at the waffle house, yeah?”

“You got it!” Dean said.

Jemma started to walk away, but stopped and turned to face Sam head on. “Oh, Sam,” she said, “I’m glad you’re enjoying yourself at your very first show.”

“Thanks, Jemma,” Sam said.

“And, I consider it the highest honor to be able to pop my boyfriend’s brother’s cherry.” She winked, and Sam shook his head, only blushing slightly this time.

Jemma didn’t return before the intermission ended, and the last four acts were a mix of musical, comedy, and one incredibly athletic dance number. He did get a kick out of some of the more outrageous drag persona’s though, and Sam definitely seemed a little taken aback by one that looked a little if Crayola put on an opera performance. Dean was pretty sure that was Mama Belle Lafitte, but he wasn’t totally sure. She’d been experimenting with show persona’s recently, so it was really anyone’s guess as to what she was going to look like from show to show. Once the lights came back on and everyone was clear to leave, Dean and Sam headed out, down towards the waffle house Dean usually met Cas and Jimmy at after one of Jimmy’s shows.

They arrived first, naturally, holding up in a booth and letting the waitress know they’d be needing for menus and coffees.

“So,” Sam asked, dumping a single creamer into his coffee cup, “that was interesting.”

Dean snorted. “Interesting good or interesting bad?”

“Good interesting. It was definitely different, though.”

“Well, yeah. What do you expect? Something tame?”

“Well, no. I guess I just wasn’t sure what to expect.”

“That’s good though,” Dean said, “keeps you on your toes.”

“Yeah, I guess. Hey! Who was that drag queen in the gold dress?”

“Ivy?”

“Yeah, I could’ve sworn I knew her from somewhere. The voice is just super familiar.”

Dean chuckled. “You remember that cop that pulled us over last fall coming back from your boyfriend’s party?” 

“No shit!”

“Yeah.”

“He was cool. He didn’t even notice the weed in the car.”

“Oh, he noticed. He still gives me shit about it sometimes, he’s just cool like that. Oh! Hey, here they come,” Dean nodded towards the door, where Cas and Jimmy were talking to the hostess. Cas, as Jimmy had mentioned before, was in a pink blouse and slacks. Jimmy was wearing a baseball shirt and blue jeans, his short hair sticking up every which way and the barest amount of glitter on his skin, glimmering in the light.

The hostess walked them over to the booth Sam and Dean were sitting at, and they sat down, Cas sliding in gradually while Jimmy just plopped down, throwing an arm over the back of the booth.

The waitress gave them a moment to sort out their order, leaving the four of them alone. Neither Cas nor Jimmy touched their menus, however. It had become enough of a routine that they didn’t need to anymore.

“Okay, Sam, you’ve met my boyfriend, Jimmy,” Dean said. Jimmy gave a goofy little salute before picking up his coffee.

“And, this is my paramour, Castiel,” Dean said.

“It’s a pleasure to meet, you, Sam,” Cas said, sticking out a hand, “Dean’s told us nothing but great things about you.”

“Thanks,” Sam said, shaking Cas’s hand, “I’ve heard good things about the both of you, too.”

“Awh, Dean talks about us,” Jimmy said, elbowing Cas in the ribs. “Oh, by the way, I didn’t embarrass you too badly today, did I? You were pretty red and I don’t wanna be that asshole. So, If I was a dick you can tell me.”

“Nah, it was okay,” Sam said. “It wasn’t the worst thing that’s ever happened. And Dean’s done worse.”

Dean looked down at the menu in front of him. He didn’t really need it, he knew what he was going to get already, he just wanted to make it less obvious that he was watching Sam and trying to gauge his reaction to things. He’d seemed pretty okay about the whole polyamory thing when he told Sam about it, but it would be harder to fake acceptance when the truth was right in front of you.

But Dean could see the cogs turning in Sam’s head and the way his eyes drifted from Jimmy’s manicured nails to the hoop earrings in Cas’s ears.

“So, uh,” Sam said, leaning in closer to Cas, “I know that when Jimmy’s doing a show it’s Jemma right? And you go by she?” Jimmy nodded, a single eyebrow raised as he sipped his coffee. “But, when you’re not it’s Jimmy. But, uh, I don’t want this to sound rude but no one has referred to you by anything other than your name so what should I use, pronoun wise, Cas?” Sam asked.

“I like this one,” Jimmy said, smiling.

“No one told you?” Cas asked.

Sam’s eyes got a little wider and he shook his head.

Cas huffed, smacking Jimmy in the arm. Jimmy just had enough time to pull the coffee cup away from his mouth so it sloshed on the table and not his lap. “What!”

“You were being rude! You should’ve said something to Sam. You knew we were supposed to meet him today and you didn’t say anything.”

Jimmy rolled his eyes, pulling a handful of napkins out of the dispenser in the center. “Sorry, Cas but I was a little busy at the time, looking for you, might I add, and I didn’t know if it was my place.”

“And what’s your excuse, Dean?” Cas asked, leveling a serious stare in his direction.

Dean threw up his hands. “I didn’t think… I didn’t know if you wanted me to tell him.”

Cas groaned. “My apologies, Sam. “She” is fine for today. I’m sorry our brothers are idiots and didn’t think to tell you.”

“In my defense, I didn’t know,” Dean said, “It’s not like everyone in the world knows.”

Cas rolled her eyes. “You could’ve told your brother that off the bat.”

“I didn’t think it was my place to tell him,” Dean said, “isn’t it rude to just, I dunno, out someone without their knowledge?”

Cas huffed. “It’s not outing if everyone knows. You told him we’re dating, and you told him you and Jimmy were dating. How is that all that different.”

“I’m sorry?” Dean said.

“Well, in his defense, it’s new to him,” Jimmy said. “He’s never dated anyone who’s not a dude before.”

Cas shook her head back and forth, bringing her cup of coffee up to her lips. “Fine. But consider this a new rule. You can your family you’re dating a genderfluid person.”

“Got it,” Dean said.

“But as for you,” Cas turned to face Jimmy, who slunk away from Cas’s gaze.

“Yeah, but he’s not my brother so… same applies?” Jimmy said.

Cas sighed. “Alright. Fine. But now that you know, Sam, she or he is fine for me. But if I tell you to use one specifically on a specific day, use that.”

“Got it,” Sam said, picking up his menu.

Dean caught the small smile Cas and Jimmy shared before the waitress returned and took their orders. They settled into the usual boring conversations after that, talking about what Cas and Jimmy did for a living and what Sam was majoring it. All in all the three of them seemed to get along really well. Sam and Cas got to talking about some literary theory after Cas mentioned she was a professor and Sam after a while Sam eventually started returning Jimmy’s lighthearted jabs.

“So, I’d been meaning to ask,” Sam said over his waffle, “how’d you wind up getting into drag, Jimmy?”

Jimmy laughed, shooting Cas a questioning glance. Cas nodded and she began to speak.

“When we were in high school I had a lot of bullies. I used to paint my nails on the weekend, but once I forgot to get rid of it before Monday morning. Several boys were not impressed. Jimmy stood up for me, and we both got our asses kicked.”

“But from then on,” Jimmy said, “I decided that no one was going to make my twin feel like shit for dressing the way she wanted. So, when Cas wore nail polish, I wore makeup. Granted, it was busted as all hell, but I was a seventeen-year-old boy so what the fuck did I know about makeup? But if Cas wore a skirt, I wore a dress. If Cas wore earrings, I wore the most ostentatious necklace and rings and earrings I could get my hands on. I still got the shit kick outta me, but I was more of a target than Cas was. And, I kinda liked the dresses. Not in the way Cas does, mind, but I’ve always been a drama queen and the performance aspect was fun. So, drag just seemed like a fun way to express myself.”

“Did they eventually stop?” Sam asked.

Jimmy snorted, “yeah, when we graduated.”

“I’m sorry,” Sam said, “that’s horseshit.”

Jimmy shrugged. “Some people just can’t accept raging queers. Fuck ‘em. They’re worse off for not knowing us as people if you ask me.”

“Still,” Sam said.

“The world is full of douchebags,” Cas said, “but it’s also full of really nice and accepting people. The bigotry of other people isn’t my problem. And I’m in a better place, now.”

“Well, I’m glad for that,” Sam said.

There was an awkward silence for a while then.

“But, you know, speaking of drag,” Jimmy said, pointing his fork at Dean, “I’ve been trying to convince this one to give it a shot. He’d be great if you ask me.”

Sam smirked. “You know, I think you might be right.”

Dean rolled his eyes but smiled. “Getting you three together was a bad idea, wasn’t it?”

“Undoubtedly,” Cas said, finishing a bite of pancake, “but now that there’s three of us we’ll get you in a dress yet.”

**Author's Note:**

> Comments and kudos are always appreciated.  
> If you wanna come yell at me, I'm over here on [tumblr](https://jamesnovakwinchester.tumblr.com/). (Nice yelling is always encouraged.)


End file.
